WO2001044492A3 - Method for kinetic resolution of racemates of alcohols or carboxylic acid esters - Google Patents

Method for kinetic resolution of racemates of alcohols or carboxylic acid esters Download PDF

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Publication number
WO2001044492A3
WO2001044492A3 PCT/DE2000/004536 DE0004536W WO0144492A3 WO 2001044492 A3 WO2001044492 A3 WO 2001044492A3 DE 0004536 W DE0004536 W DE 0004536W WO 0144492 A3 WO0144492 A3 WO 0144492A3
Authority
WO
WIPO (PCT)
Prior art keywords
alcohols
carboxylic acid
acid esters
racemates
kinetic resolution
Prior art date
Application number
PCT/DE2000/004536
Other languages
German (de)
French (fr)
Other versions
WO2001044492A2 (en
Inventor
Fritz Theil
Helmut Sonnenschein
Original Assignee
Asca Gmbh
Inst Nichtklassische Chemie E
Fritz Theil
Helmut Sonnenschein
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE19963315A external-priority patent/DE19963315A1/en
Priority claimed from DE19963314A external-priority patent/DE19963314A1/en
Priority claimed from DE2000106824 external-priority patent/DE10006824A1/en
Application filed by Asca Gmbh, Inst Nichtklassische Chemie E, Fritz Theil, Helmut Sonnenschein filed Critical Asca Gmbh
Priority to AU30011/01A priority Critical patent/AU3001101A/en
Priority to EP00990552A priority patent/EP1242613A2/en
Publication of WO2001044492A2 publication Critical patent/WO2001044492A2/en
Publication of WO2001044492A3 publication Critical patent/WO2001044492A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
    • C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Zoology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Analytical Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to a method of kinetic resolution of racemates of alcohols or carboxylic acid esters. Fluorine phase marking of the quicker or more slowly reacting enantiomer is obtained by lipase-catalysed reaction of racemic alcohols with fluorinated carboxylic acid esters of racemic alcohols with water. The enantiomers are then extractively separated by division between an organic and a fluorine phase.
PCT/DE2000/004536 1999-12-19 2000-12-18 Method for kinetic resolution of racemates of alcohols or carboxylic acid esters WO2001044492A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU30011/01A AU3001101A (en) 1999-12-19 2000-12-18 Method for kinetic resolution of racemates of alcohols or carboxylic acid esters
EP00990552A EP1242613A2 (en) 1999-12-19 2000-12-18 Method for kinetic resolution of racemates of alcohols or carboxylic acid esters

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
DE19963315.0 1999-12-19
DE19963314.2 1999-12-19
DE19963315A DE19963315A1 (en) 1999-12-19 1999-12-19 Resolution of racemic alcohols and carboxylic acid esters involves lipase catalyzed labeling of one enantiomer with fluorine to improve enantiomer separation procedure
DE19963314A DE19963314A1 (en) 1999-12-19 1999-12-19 Resolution of racemic alcohols and carboxylic acid esters involves lipase catalyzed labeling of one enantiomer with fluorine to improve enantiomer separation procedure
DE2000106824 DE10006824A1 (en) 2000-02-08 2000-02-08 Resolution of racemic alcohols and carboxylic acid esters involves lipase catalyzed labeling of one enantiomer with fluorine to improve enantiomer separation procedure
DE10006824.3 2000-02-08

Publications (2)

Publication Number Publication Date
WO2001044492A2 WO2001044492A2 (en) 2001-06-21
WO2001044492A3 true WO2001044492A3 (en) 2002-01-31

Family

ID=27213660

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/DE2000/004536 WO2001044492A2 (en) 1999-12-19 2000-12-18 Method for kinetic resolution of racemates of alcohols or carboxylic acid esters

Country Status (4)

Country Link
US (1) US20030003552A1 (en)
EP (1) EP1242613A2 (en)
AU (1) AU3001101A (en)
WO (1) WO2001044492A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7214819B2 (en) * 2001-06-08 2007-05-08 Fluorous Technologies, Inc. Fluorous triphasic reaction and separation processes for the generation of enantioenriched alcohols, amines, carboxylic acids and related compounds
DE10164269A1 (en) * 2001-12-19 2003-07-03 Asca Gmbh Angewandte Synthesec Process for the kinetic resolution of alcohols with one or more stereogenic centers
DE10248166A1 (en) * 2002-10-16 2004-06-17 Bayer Ag Anti-Kazlauskas lipases

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
LEMKE K ET AL: "Lipase-catalysed Kinetic Resolution of Phenylethan-1,2-diol by Sequential Transesterification - the Influence of the Solvent", TETRAHEDRON: ASYMMETRY,NL,ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, vol. 7, no. 4, 1 April 1996 (1996-04-01), pages 971 - 974, XP004047759, ISSN: 0957-4166 *
STEAD P ET AL: "Efficient procedures for the large-scale preparation of (1S,2S)-trans-2-methoxycyclohexanol, a key chiral intermediate in the synthesis of tricyclic beta-lactam antibiotics", TETRAHEDRON: ASYMMETRY,NL,ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, vol. 7, no. 8, 1 August 1996 (1996-08-01), pages 2247 - 2250, XP004048280, ISSN: 0957-4166 *
THEIL F ET AL: "Lipase-catalysed Resolution of 3,3'-Bi-indolizines: The First Preparative Access to Enantiomerically Pure Samples", TETRAHEDRON: ASYMMETRY, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, vol. 7, no. 12, 1 December 1996 (1996-12-01), pages 3365 - 3370, XP004070811, ISSN: 0957-4166 *
THEIL FRITZ ET AL: "Kinetic resolution of acyclic 1,2-diols using a sequential lipase-catalyzed transesterification in organic solvents.", JOURNAL OF ORGANIC CHEMISTRY, vol. 59, no. 2, 1994, pages 388 - 393, XP002173755, ISSN: 0022-3263 *

Also Published As

Publication number Publication date
AU3001101A (en) 2001-06-25
WO2001044492A2 (en) 2001-06-21
US20030003552A1 (en) 2003-01-02
EP1242613A2 (en) 2002-09-25

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